메뉴 건너뛰기




Volumn 8, Issue 2, 2013, Pages 325-344

Synthesis of 9-amino(9-deoxy)epi cinchona alkaloids, general chiral organocatalysts for the stereoselective functionalization of carbonyl compounds

Author keywords

[No Author keywords available]

Indexed keywords

9 AMINO (9 DEOXY)EPICINCHONA ALKALOID; CARBONYL DERIVATIVE; CINCHONA ALKALOID; HYDROQUININE; QUINIDINE; QUININE; UNCLASSIFIED DRUG;

EID: 84873342799     PISSN: 17542189     EISSN: 17502799     Source Type: Journal    
DOI: 10.1038/nprot.2012.155     Document Type: Article
Times cited : (61)

References (66)
  • 1
    • 77749298554 scopus 로고    scopus 로고
    • Emil Knoevenagel and the roots of aminocatalysis
    • List, B. Emil Knoevenagel and the roots of aminocatalysis. Angew. Chem. Int. Ed. 49, 1730-1734 (2010).
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 1730-1734
    • List, B.1
  • 3
    • 67549137639 scopus 로고    scopus 로고
    • Asymmetric catalysis with chiral primary aminebased organocatalysts
    • Xu, L.-W., Luo, J. & Lu, Y. Asymmetric catalysis with chiral primary aminebased organocatalysts. Chem. Commun. 14, 1807-1821 (2009).
    • (2009) Chem. Commun. , vol.14 , pp. 1807-1821
    • Xu, L.-W.1    Luo, J.2    Lu, Y.3
  • 5
    • 0037043180 scopus 로고    scopus 로고
    • Proline-catalyzed asymmetric reactions
    • List, B. Proline-catalyzed asymmetric reactions. Tetrahedron 58, 5573-5590 (2002).
    • (2002) Tetrahedron , vol.58 , pp. 5573-5590
    • List, B.1
  • 6
    • 33745715054 scopus 로고    scopus 로고
    • Modern strategies in organic catalysis: The advent and development of iminium activation
    • Lelais, G. & MacMillan, D.W.C. Modern strategies in organic catalysis: the advent and development of iminium activation. Aldrichimica Acta 39, 79-87 (2006).
    • (2006) Aldrichimica Acta , vol.39 , pp. 79-87
    • Lelais, G.1    MacMillan, D.W.C.2
  • 7
    • 0034654216 scopus 로고    scopus 로고
    • Proline-catalyzed direct asymmetric aldol reactions
    • List, B., Lerner, R.A. & Barbas, C.F. Proline-catalyzed direct asymmetric aldol reactions. J. Am. Chem. Soc. 122, 2395-2396 (2000).
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 2395-2396
    • List, B.1    Lerner, R.A.2    Barbas, C.F.3
  • 8
    • 0034600250 scopus 로고    scopus 로고
    • New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction
    • Ahrendt, K.A., Borths, C.J. & MacMillan, D.W.C. New strategies for organic catalysis: the first highly enantioselective organocatalytic Diels-Alder reaction. J. Am. Chem. Soc. 122, 4243-4244 (2000).
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 4243-4244
    • Ahrendt, K.A.1    Borths, C.J.2    MacMillan, D.W.C.3
  • 9
    • 33749527371 scopus 로고    scopus 로고
    • Dienamine catalysis: Organocatalytic asymmetric amination of unsaturated aldehydes
    • Bertelsen, S., Marigo, M., Brandes, S., Diner, P. & Jorgensen, K.A. Dienamine catalysis: organocatalytic asymmetric amination of unsaturated aldehydes. J. Am. Chem. Soc. 128, 12973-12980 (2006).
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 12973-12980
    • Bertelsen, S.1    Marigo, M.2    Brandes, S.3    Diner, P.4    Jorgensen, K.A.5
  • 10
    • 79953845548 scopus 로고    scopus 로고
    • Trienamines in asymmetric organocatalysis: Diels-Alder and tandem reactions
    • Jia, Z.-J. et al. Trienamines in asymmetric organocatalysis: Diels-Alder and tandem reactions. J. Am. Chem. Soc. 133, 5053-5061 (2011).
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 5053-5061
    • Jia, Z.-J.1
  • 11
    • 79957563809 scopus 로고    scopus 로고
    • Recent advances in asymmetric catalysis with cinchona alkaloid-based primary amines
    • Jiang, L. & Chen, Y.-C. Recent advances in asymmetric catalysis with cinchona alkaloid-based primary amines. Catal. Sci. Technol. 1, 354-365 (2011).
    • (2011) Catal. Sci. Technol. , vol.1 , pp. 354-365
    • Jiang, L.1    Chen, Y.-C.2
  • 12
    • 48349106907 scopus 로고    scopus 로고
    • A novel organocatalytic tool for the iminium activation of unsaturated ketones
    • Bartoli, G. & Melchiorre, P. A novel organocatalytic tool for the iminium activation of unsaturated ketones. Synlett 1759-1772 (2008).
    • (2008) Synlett , pp. 1759-1772
    • Bartoli, G.1    Melchiorre, P.2
  • 13
    • 79951851693 scopus 로고    scopus 로고
    • Easy access to 9-epimers of cinchona alkaloids: One-pot inversion by Mitsunobu esterification-saponification
    • Sidorowicz, A. & Skarewski, J. Easy access to 9-epimers of cinchona alkaloids: one-pot inversion by Mitsunobu esterification-saponification. Synthesis 708-710 (2011).
    • (2011) Synthesis , pp. 708-710
    • Sidorowicz, A.1    Skarewski, J.2
  • 14
    • 33744825692 scopus 로고    scopus 로고
    • Efficient iridium and rhodium-catalyzed asymmetric transfer hydrogenation using 9-amino (9-deoxy) cinchona alkaloids as chiral ligands
    • He, W., Liu, P., Zhang, B.L., Sun, X.L. & Zhang, S.Y. Efficient iridium and rhodium-catalyzed asymmetric transfer hydrogenation using 9-amino (9-deoxy) cinchona alkaloids as chiral ligands. Appl. Organomet. Chem. 20, 328-334 (2006).
    • (2006) Appl. Organomet. Chem. , vol.20 , pp. 328-334
    • He, W.1    Liu, P.2    Zhang, B.L.3    Sun, X.L.4    Zhang, S.Y.5
  • 15
    • 0029161459 scopus 로고
    • Enantioselective catalysis 98.Preparation of 9-amino-(9-deoxy)cinchona alkaloids
    • Brunner, H., Bugler, J. & Nuber, B. Enantioselective catalysis 98. Preparation of 9-amino-(9-deoxy)cinchona alkaloids. Tetrahedron Asymmetry 6, 1699-1702 (1995).
    • (1995) Tetrahedron Asymmetry , vol.6 , pp. 1699-1702
    • Brunner, H.1    Bugler, J.2    Nuber, B.3
  • 16
    • 0037255614 scopus 로고    scopus 로고
    • Synthesis of 9-N-cinchona alkaloid peptide hybrid derivatives: Preparation and conformational study of 9-N-acylamino(9-deoxy)cinchona alkaloids
    • Sundermeier, U., Dobler, C., Mehltretter, G.M., Baumann, W. & Beller, M. Synthesis of 9-N-cinchona alkaloid peptide hybrid derivatives: preparation and conformational study of 9-N-acylamino(9-deoxy)cinchona alkaloids. Chirality 15, 127-134 (2003).
    • (2003) Chirality , vol.15 , pp. 127-134
    • Sundermeier, U.1    Dobler, C.2    Mehltretter, G.M.3    Baumann, W.4    Beller, M.5
  • 17
    • 19544393388 scopus 로고    scopus 로고
    • Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts
    • Vakulya, B., Varga, S., Csampai, A. & Soos, T. Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts. Org. Lett. 7, 1967-1969 (2005).
    • (2005) Org. Lett. , vol.7 , pp. 1967-1969
    • Vakulya, B.1    Varga, S.2    Csampai, A.3    Soos, T.4
  • 18
    • 33749450914 scopus 로고    scopus 로고
    • Synthesis of chiral diamine ligands derived from cinchona alkaloids and their catalytic performance for asymmetric transfer hydrogenation
    • He, W., Zhang, B., Liu, P., Sun, X. & Zhang, S. Synthesis of chiral diamine ligands derived from cinchona alkaloids and their catalytic performance for asymmetric transfer hydrogenation. Chin. J. Catal. 27, 527-531 (2006).
    • (2006) Chin. J. Catal. , vol.27 , pp. 527-531
    • He, W.1    Zhang, B.2    Liu, P.3    Sun, X.4    Zhang, S.5
  • 19
    • 33847793920 scopus 로고    scopus 로고
    • Readily accessible 9-epi-amino cinchona alkaloid derivatives promote efficient, highly enantioselective additions of aldehydes and ketones to nitroolefins
    • McCooey, S.H. & Connon, S.J. Readily accessible 9-epi-amino cinchona alkaloid derivatives promote efficient, highly enantioselective additions of aldehydes and ketones to nitroolefins. Org. Lett. 9, 599-602 (2007).
    • (2007) Org. Lett. , vol.9 , pp. 599-602
    • McCooey, S.H.1    Connon, S.J.2
  • 20
    • 84866492507 scopus 로고    scopus 로고
    • Cinchona-based primary amine catalysis in the asymmetric functionalization of carbonyl compounds
    • Melchiorre, P. Cinchona-based primary amine catalysis in the asymmetric functionalization of carbonyl compounds. Angew. Chem. Int. Ed. 51, 9748-9770 (2012).
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 9748-9770
    • Melchiorre, P.1
  • 21
    • 34147174295 scopus 로고    scopus 로고
    • Organocatalytic asymmetric Friedel-Crafts alkylation of indoles with simple unsaturated ketones
    • Bartoli, G. et al. Organocatalytic asymmetric Friedel-Crafts alkylation of indoles with simple unsaturated ketones. Org. Lett. 9, 1403-1405 (2007).
    • (2007) Org. Lett. , vol.9 , pp. 1403-1405
    • Bartoli, G.1
  • 22
    • 54749123572 scopus 로고    scopus 로고
    • Asymmetric aza-Michael reactions of unsaturated ketones with bifunctional organic catalysts
    • Lu, X. & Deng, L. Asymmetric aza-Michael reactions of unsaturated ketones with bifunctional organic catalysts. Angew. Chem. Int. Ed. 47, 7710-7713 (2008).
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 7710-7713
    • Lu, X.1    Deng, L.2
  • 23
    • 46049099172 scopus 로고    scopus 로고
    • Catalytic enantioselective peroxidation of unsaturated ketones
    • Lu, X., Liu, Y., Sun, B., Cindric, B. & Deng, L. Catalytic enantioselective peroxidation of unsaturated ketones. J. Am. Chem. Soc. 130, 8134-8135 (2008).
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 8134-8135
    • Lu, X.1    Liu, Y.2    Sun, B.3    Cindric, B.4    Deng, L.5
  • 25
    • 55249110210 scopus 로고    scopus 로고
    • Organocatalytic asymmetric aziridination of enones
    • Pesciaioli, F. et al. Organocatalytic asymmetric aziridination of enones. Angew. Chem. Int. Ed. 47, 8703-8706 (2008).
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 8703-8706
    • Pesciaioli, F.1
  • 26
    • 77954342292 scopus 로고    scopus 로고
    • Asymmetric catalytic aziridination of cyclic enones
    • De Vincentiis, F et al. Asymmetric catalytic aziridination of cyclic enones. Chem. Asian J. 5, 1652-1656 (2010).
    • (2010) Chem. Asian J. , vol.5 , pp. 1652-1656
    • De Vincentiis1    Et Al, F.2
  • 27
    • 70350061735 scopus 로고    scopus 로고
    • Organocatalytic asymmetric vinylogous ketol rearrangement: Enantioselective construction of chiral all-carbon quaternary stereocenters in spirocyclic diketones via semipinacol-type 1,2-carbon migration
    • Zhang, E., Fan, C.-A., Tu, Y.-Q., Zhang, F.-M. & Song, Y.-L. Organocatalytic asymmetric vinylogous ketol rearrangement: enantioselective construction of chiral all-carbon quaternary stereocenters in spirocyclic diketones via semipinacol-type 1,2-carbon migration. J. Am. Chem. Soc. 131, 14626-14627 (2009).
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 14626-14627
    • Zhang, E.1    Fan, C.-A.2    Tu, Y.-Q.3    Zhang, F.-M.4    Song, Y.-L.5
  • 28
    • 77955034318 scopus 로고    scopus 로고
    • Catalytic asymmetric epoxidation of branched enals
    • Lifchits, O., Reisinger, C.M. & List, B. Catalytic asymmetric epoxidation of branched enals. J. Am. Chem. Soc. 132, 10227-10229 (2010).
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 10227-10229
    • Lifchits, O.1    Reisinger, C.M.2    List, B.3
  • 29
    • 58449101797 scopus 로고    scopus 로고
    • Enantioselective synthesis of functionalized nitrocyclopropanes by organocatalytic conjugate addition of bromonitroalkanes to unsaturated enones
    • Lv, J., Zhang, J., Lin, Z. & Wang, Y. Enantioselective synthesis of functionalized nitrocyclopropanes by organocatalytic conjugate addition of bromonitroalkanes to unsaturated enones. Chem. Eur. J. 15, 972-979 (2009).
    • (2009) Chem. Eur. J. , vol.15 , pp. 972-979
    • Lv, J.1    Zhang, J.2    Lin, Z.3    Wang, Y.4
  • 30
    • 54649084880 scopus 로고    scopus 로고
    • Primary-amine-catalyzed enantioselective intramolecular aldolizations
    • Zhou, J., Wakchaure, V., Kraft, P. & List, B. Primary-amine-catalyzed enantioselective intramolecular aldolizations. Angew. Chem. Int. Ed. 47, 7656-7658 (2008).
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 7656-7658
    • Zhou, J.1    Wakchaure, V.2    Kraft, P.3    List, B.4
  • 31
    • 70349784950 scopus 로고    scopus 로고
    • Targeting structural and stereochemical complexity by organocascade catalysis: Construction of spirocyclic oxindoles having multiple stereocenters
    • Bencivenni, G. et al. Targeting structural and stereochemical complexity by organocascade catalysis: construction of spirocyclic oxindoles having multiple stereocenters. Angew. Chem. Int. Ed. 48, 7200-7203 (2009).
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 7200-7203
    • Bencivenni, G.1
  • 32
    • 70349786290 scopus 로고    scopus 로고
    • Organocascade reactions of enones catalyzed by a chiral primary amine
    • Wu, L.-Y. et al. Organocascade reactions of enones catalyzed by a chiral primary amine. Angew. Chem. Int. Ed. 48, 7196-7199 (2009).
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 7196-7199
    • Wu, L.-Y.1
  • 34
    • 78650570854 scopus 로고    scopus 로고
    • Direct asymmetric vinylogous Michael addition of cyclic enones to nitroalkenes via dienamine catalysis
    • Bencivenni, G., Galzerano, P., Mazzanti, A., Bartoli, G. & Melchiorre, P. Direct asymmetric vinylogous Michael addition of cyclic enones to nitroalkenes via dienamine catalysis. Proc. Natl. Acad. Sci. USA 107, 20642-20647 (2010).
    • (2010) Proc. Natl. Acad. Sci. USA , vol.107 , pp. 20642-20647
    • Bencivenni, G.1    Galzerano, P.2    Mazzanti, A.3    Bartoli, G.4    Melchiorre, P.5
  • 35
    • 78650090073 scopus 로고    scopus 로고
    • Cooperative organocatalysis for the asymmetric alkylation of branched enals
    • Bergonzini, G., Vera, S. & Melchiorre, P. Cooperative organocatalysis for the asymmetric alkylation of branched enals. Angew. Chem. Int. Ed. 49, 9685-9688 (2010).
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 9685-9688
    • Bergonzini, G.1    Vera, S.2    Melchiorre, P.3
  • 36
    • 84860119030 scopus 로고    scopus 로고
    • Trienamine catalysis with 2,4-dienones: Development and application in asymmetric Diels-Alder reactions
    • Xiong, X.-F. et al. Trienamine catalysis with 2,4-dienones: development and application in asymmetric Diels-Alder reactions. Angew. Chem. Int. Ed. 51, 4401-4404 (2012).
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 4401-4404
    • Xiong, X.-F.1
  • 38
    • 44349168328 scopus 로고    scopus 로고
    • Asymmetric catalysis with bifunctional cinchona alkaloidbased urea and thiourea organocatalysts
    • Connon, S.J. Asymmetric catalysis with bifunctional cinchona alkaloidbased urea and thiourea organocatalysts. Chem. Commun. 14, 2499-2510 (2008).
    • (2008) Chem. Commun. , vol.14 , pp. 2499-2510
    • Connon, S.J.1
  • 39
    • 80455178516 scopus 로고    scopus 로고
    • Diastereodivergent asymmetric sulfa-Michael additions of branched enones using a single chiral organic catalyst
    • Tian, X. et al. Diastereodivergent asymmetric sulfa-Michael additions of branched enones using a single chiral organic catalyst. J. Am. Chem. Soc. 133, 17934-17941 (2011).
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 17934-17941
    • Tian, X.1
  • 40
    • 0024343737 scopus 로고
    • Conformational study of cinchona alkaloids. A combined NMR, molecular mechanics and X-ray approach
    • Dijkstra, G.D.H. et al. Conformational study of cinchona alkaloids. A combined NMR, molecular mechanics and X-ray approach. J. Am. Chem. Soc. 111, 8069-8076 (1989).
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8069-8076
    • Dijkstra, G.D.H.1
  • 41
    • 85077634689 scopus 로고
    • The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products
    • Mitsunobu, O. The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis 1-28 (1981).
    • (1981) Synthesis , pp. 1-28
    • Mitsunobu, O.1
  • 42
    • 67649386488 scopus 로고    scopus 로고
    • Mitsunobu and related reactions: Advances and applications
    • Swamy, K.C.K., Kumar, N.N.B., Balaraman, E. & Kumar, K.V.P.P. Mitsunobu and related reactions: advances and applications. Chem. Rev. 109, 2551-2651 (2009).
    • (2009) Chem. Rev. , vol.109 , pp. 2551-2651
    • Swamy, K.C.K.1    Kumar, N.N.B.2    Balaraman, E.3    Kumar, K.V.P.P.4
  • 43
    • 0030941221 scopus 로고    scopus 로고
    • Application of the Mitsunobu reaction in the field of alkaloids
    • Simon, C., Hosztafi, S. & Makleit, S. Application of the Mitsunobu reaction in the field of alkaloids. J. Heterocyclic Chem. 34, 349-365 (1997).
    • (1997) J. Heterocyclic Chem. , vol.34 , pp. 349-365
    • Simon, C.1    Hosztafi, S.2    Makleit, S.3
  • 44
    • 84977258365 scopus 로고
    • Ueber neue organische Phosphorverbindungen II. Phosphazine
    • Staudinger, H. & Meyer, J. Ueber neue organische Phosphorverbindungen II. Phosphazine. Helv. Chim. Acta 2, 619-635 (1919).
    • (1919) Helv. Chim. Acta , vol.2 , pp. 619-635
    • Staudinger, H.1    Meyer, J.2
  • 45
    • 33645455231 scopus 로고    scopus 로고
    • Dual-function cinchona alkaloid catalysis: Catalytic asymmetric tandem conjugate additionprotonation for the direct creation of nonadjacent stereocenters
    • Wang, Y., Liu, X. & Deng, L. Dual-function cinchona alkaloid catalysis: catalytic asymmetric tandem conjugate additionprotonation for the direct creation of nonadjacent stereocenters. J. Am. Chem. Soc. 128, 3928-3930 (2006).
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 3928-3930
    • Wang, Y.1    Liu, X.2    Deng, L.3
  • 46
    • 35048856888 scopus 로고    scopus 로고
    • Enantioselective 1,3-dipolar cycloaddition of cyclic enones catalyzed by multifunctional primary amines: Beneficial effects of hydrogen bonding
    • Chen, W. et al. Enantioselective 1,3-dipolar cycloaddition of cyclic enones catalyzed by multifunctional primary amines: Beneficial effects of hydrogen bonding. Angew. Chem. Int. Ed. 46, 7667-7670 (2007).
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 7667-7670
    • Chen, W.1
  • 47
    • 0026418434 scopus 로고
    • The atom economy-A search for synthetic efficiency
    • Trost, B. The atom economy-a search for synthetic efficiency. Science 254, 1471-1477 (1991).
    • (1991) Science , vol.254 , pp. 1471-1477
    • Trost, B.1
  • 48
    • 0031482354 scopus 로고    scopus 로고
    • An efficient large-scale synthesis of methyl 5-[2-(2,5-dimethoxyphenyl) ethyl]-2-hydroxybenzoate
    • Kucerovy, A., Li, T., Prasad, K., Repic, O. & Blacklock, T.J. An efficient large-scale synthesis of methyl 5-[2-(2,5-dimethoxyphenyl)ethyl]-2- hydroxybenzoate. Org. Process Res. Dev. 1, 287-293 (1997).
    • (1997) Org. Process Res. Dev. , vol.1 , pp. 287-293
    • Kucerovy, A.1    Li, T.2    Prasad, K.3    Repic, O.4    Blacklock, T.J.5
  • 49
    • 0037358014 scopus 로고    scopus 로고
    • Rapid development of an enantioselective synthesis of (R)-1-hydroxy-7-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid
    • Ainge, D., Ennis, D., Gidlund, M., Stefinovic, M. & Vaz, L.-M. Rapid development of an enantioselective synthesis of (R)-1-hydroxy-7-methoxy-1,2,3,4- tetrahydronaphthalene-1-carboxylic acid. Org. Process Res. Dev. 7, 198-201 (2003).
    • (2003) Org. Process Res. Dev. , vol.7 , pp. 198-201
    • Ainge, D.1    Ennis, D.2    Gidlund, M.3    Stefinovic, M.4    Vaz, L.-M.5
  • 50
    • 0141993866 scopus 로고    scopus 로고
    • A practical synthesis of 6-[2-(2,5-dimethoxyphenyl)ethyl]-4- ethylquinazoline and the art of removing palladium from the products of Pd-catalyzed reactions
    • Konigsberger, K. et al. A practical synthesis of 6-[2-(2,5- dimethoxyphenyl)ethyl]-4-ethylquinazoline and the art of removing palladium from the products of Pd-catalyzed reactions. Org. Process Res. Dev. 7, 733-742 (2003).
    • (2003) Org. Process Res. Dev. , vol.7 , pp. 733-742
    • Konigsberger, K.1
  • 51
    • 11144358642 scopus 로고    scopus 로고
    • The first and second cinchona rearrangement. two fundamental transformations of alkaloid chemistry
    • Franz, M.H., Roper, S., Wartchow, R. & Hoffmann, H.M.R. The first and second cinchona rearrangement. two fundamental transformations of alkaloid chemistry. J. Org. Chem. 69, 2983-2991 (2004).
    • (2004) J. Org. Chem. , vol.69 , pp. 2983-2991
    • Franz, M.H.1    Roper, S.2    Wartchow, R.3    Hoffmann, H.M.R.4
  • 52
    • 78649831810 scopus 로고    scopus 로고
    • Clickable 9-azido-(9-deoxy)-cinchona alkaloids: Synthesis and conformation
    • Kacprzak, K. & Gierczyk, B. Clickable 9-azido-(9-deoxy)-cinchona alkaloids: synthesis and conformation. Tetrahedron Asymmetry 21, 2740-2745 (2010).
    • (2010) Tetrahedron Asymmetry , vol.21 , pp. 2740-2745
    • Kacprzak, K.1    Gierczyk, B.2
  • 53
    • 4544252293 scopus 로고    scopus 로고
    • Asymmetric synthesis of 2-amino-1,3-diols and d-erythro-Sphinganine
    • Enders, D. & Muller-Huwen, A. Asymmetric synthesis of 2-amino-1,3-diols and d-erythro-Sphinganine. Eur. J. Org. Chem 2004, 1732-1739 (2004).
    • (2004) Eur. J. Org. Chem , vol.2004 , pp. 1732-1739
    • Enders, D.1    Muller-Huwen, A.2
  • 54
    • 10644254681 scopus 로고    scopus 로고
    • A substrate mimetic approach for influenza neuraminidase inhibitors
    • Jeong, J.W. et al. A substrate mimetic approach for influenza neuraminidase inhibitors. Bull. Korean Chem. Soc. 25, 1575-1577 (2004).
    • (2004) Bull. Korean Chem. Soc. , vol.25 , pp. 1575-1577
    • Jeong, J.W.1
  • 55
    • 33847684381 scopus 로고    scopus 로고
    • Carbohydrate mimic of 2-deoxystreptamine for the preparation of conformationally constrained aminoglycosides
    • Busscher, G.F., van den Broek, S.A.M.W., Rutjes, F.P.J.T. & van Delft, F.L. Carbohydrate mimic of 2-deoxystreptamine for the preparation of conformationally constrained aminoglycosides. Tetrahedron 63, 3183-3188 (2007).
    • (2007) Tetrahedron , vol.63 , pp. 3183-3188
    • Busscher, G.F.1    Van Den Broek, S.A.M.W.2    Rutjes, F.P.J.T.3    Van Delft, F.L.4
  • 56
    • 76149095638 scopus 로고    scopus 로고
    • Synthesis of amino-bridged oligosaccharide mimetics
    • Neumann, J. & Thiem, J. Synthesis of amino-bridged oligosaccharide mimetics. Eur. J. Org. Chem. 2010, 900-908 (2010).
    • (2010) Eur. J. Org. Chem. , vol.2010 , pp. 900-908
    • Neumann, J.1    Thiem, J.2
  • 57
    • 46249124540 scopus 로고    scopus 로고
    • Practical demethylation of aryl methyl ethers using an odorless thiol reagent
    • Chae, J. Practical demethylation of aryl methyl ethers using an odorless thiol reagent. Arch. Pharm. Res. 31, 305-309 (2008).
    • (2008) Arch. Pharm. Res. , vol.31 , pp. 305-309
    • Chae, J.1
  • 58
    • 77949287444 scopus 로고    scopus 로고
    • Asymmetric synthesis of a potent, aminopiperidine-fused imidazopyridine dipeptidyl peptidase IV inhibitor
    • Xu, F. et al. Asymmetric synthesis of a potent, aminopiperidine-fused imidazopyridine dipeptidyl peptidase IV inhibitor. J. Org. Chem. 75, 1343-1353 (2010).
    • (2010) J. Org. Chem. , vol.75 , pp. 1343-1353
    • Xu, F.1
  • 59
    • 24044531286 scopus 로고    scopus 로고
    • Organic azides: An exploding diversity of a unique class of compounds
    • Brase, S., Gil, C., Knepper, K. & Zimmermann, V. Organic azides: an exploding diversity of a unique class of compounds. Angew. Chem. Int. Ed. 44, 5188-5240 (2005).
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 5188-5240
    • Brase, S.1    Gil, C.2    Knepper, K.3    Zimmermann, V.4
  • 60
  • 61
    • 0842285267 scopus 로고    scopus 로고
    • Large-scale synthesis of the anti-cancer marine natural product (+)-discodermolide.Part 1: Synthetic strategy and preparation of a common precursor
    • Mickel, S.J. et al. Large-scale synthesis of the anti-cancer marine natural product (+)-discodermolide. Part 1: Synthetic strategy and preparation of a common precursor. Org. Process Res. Dev. 8, 92-100 (2003).
    • (2003) Org. Process Res. Dev. , vol.8 , pp. 92-100
    • Mickel, S.J.1
  • 62
    • 65949090271 scopus 로고    scopus 로고
    • Improved synthesis of 1-(azidomethyl)-3,5-bis-(trifluoromethyl)benzene: Development of batch and microflow azide processes
    • Kopach, M.E., Murray, M.M., Braden, T.M., Kobierski, M.E. & Williams, O.L. Improved synthesis of 1-(azidomethyl)-3,5-bis-(trifluoromethyl)benzene: development of batch and microflow azide processes. Org. Process Res. Dev. 13, 152-160 (2009).
    • (2009) Org. Process Res. Dev. , vol.13 , pp. 152-160
    • Kopach, M.E.1    Murray, M.M.2    Braden, T.M.3    Kobierski, M.E.4    Williams, O.L.5
  • 65
    • 58149117465 scopus 로고    scopus 로고
    • Safety notables: Information from the literature
    • am Ende, D.J. & Vogt, P.F. Safety notables: information from the literature. Org. Process Res. Dev. 8, 1045-1048 (2004).
    • (2004) Org. Process Res. Dev. , vol.8 , pp. 1045-1048
    • Am Ende, D.J.1    Vogt, P.F.2
  • 66
    • 0039473194 scopus 로고    scopus 로고
    • Dimethoxyethane as an alternative solvent for Schmidt reactions.Preparation of homochiral N-(5-oxazolyl)oxazolidinones from N-acetoacetyl derivatives of oxazolidinones
    • Galvez, N., Moreno-Manas, M., Sebastian, R.M. & Vallribera, A. Dimethoxyethane as an alternative solvent for Schmidt reactions. Preparation of homochiral N-(5-oxazolyl)oxazolidinones from N-acetoacetyl derivatives of oxazolidinones. Tetrahedron 52, 1609-1616 (1996).
    • (1996) Tetrahedron , vol.52 , pp. 1609-1616
    • Galvez, N.1    Moreno-Manas, M.2    Sebastian, R.M.3    Vallribera, A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.